3-(Adamantan-1-ylcarbamoylethynyl)-1-benzenesulfonyl-4,6-dichloro-1H-indole-2-carboxylic acid ethyl ester | 159054-25-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 3-(Adamantan-1-ylcarbamoylethynyl)-1-benzenesulfonyl-4,6-dichloro-1H-indole-2-carboxylic acid ethyl ester
• 英文别名: Ethyl 3-[3-(1-adamantylamino)-3-oxoprop-1-ynyl]-1-(benzenesulfonyl)-4,6-dichloroindole-2-carboxylate
• CAS: 159054-25-8
• 化学式: C₃₀H₂₈Cl₂N₂O₅S
• 分子量: 599.535
• InChiKey: VMGWTDCVFKESIJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  40
• 可旋转键数：
  7
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  103
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(Adamantan-1-ylcarbamoylethynyl)-1-benzenesulfonyl-4,6-dichloro-1H-indole-2-carboxylic acid ethyl ester 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 生成 Ethyl 3-(2'-(1-Adamantylcarbamoyl)-ethynyl)-4,6-dichloroindole-2-carboxylate
  参考文献：
  名称：

  New Synthesis of Substituted 2-Carboxyindole Derivatives: Versatile Introduction of a Carbamoylethynyl Moiety at the C-3 Position

  摘要：

  A novel series of 3-carbamoylethynyl-2-carboxyindoles, antagonists acting at the strychnine-insensitive glycine binding site associated with the NMDA receptor, has been synthesised. This new versatile approach involves the introduction of a 2-chloroethenyl moiety in position C-3 with subsequent derivatisation of the terminal carboxyl group, followed by an unusual elimination of HCl to afford the ethynyl functionality. This novel series of glycine antagonists was evaluated in terms of in vitro affinity at the glycine bindings site and the most potent compound was tested in vivo in the NMDA-induced convulsions model in mice.

  DOI：

  10.1002/(sici)1521-4184(19993)332:2<55::aid-ardp55>3.0.co;2-z
• 作为产物：
  描述：

  3-[(Z)-2-(Adamantan-1-ylcarbamoyl)-2-chloro-vinyl]-1-benzenesulfonyl-4,6-dichloro-1H-indole-2-carboxylic acid ethyl ester 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 生成 3-(Adamantan-1-ylcarbamoylethynyl)-1-benzenesulfonyl-4,6-dichloro-1H-indole-2-carboxylic acid ethyl ester
  参考文献：
  名称：

  New Synthesis of Substituted 2-Carboxyindole Derivatives: Versatile Introduction of a Carbamoylethynyl Moiety at the C-3 Position

  摘要：

  A novel series of 3-carbamoylethynyl-2-carboxyindoles, antagonists acting at the strychnine-insensitive glycine binding site associated with the NMDA receptor, has been synthesised. This new versatile approach involves the introduction of a 2-chloroethenyl moiety in position C-3 with subsequent derivatisation of the terminal carboxyl group, followed by an unusual elimination of HCl to afford the ethynyl functionality. This novel series of glycine antagonists was evaluated in terms of in vitro affinity at the glycine bindings site and the most potent compound was tested in vivo in the NMDA-induced convulsions model in mice.

  DOI：

  10.1002/(sici)1521-4184(19993)332:2<55::aid-ardp55>3.0.co;2-z

文献信息

• US5686461A
  申请人：——

  公开号：US5686461A

  公开（公告）日：1997-11-11
• New Synthesis of Substituted 2-Carboxyindole Derivatives: Versatile Introduction of a Carbamoylethynyl Moiety at the C-3 Position
  作者：Cheryl T. Hewkin、Romano Di Fabio、Nadia Conti、Alfredo Cugola、Paola Gastaldi、Fabrizio Micheli、Anna M. Quaglia

  DOI：10.1002/(sici)1521-4184(19993)332:2<55::aid-ardp55>3.0.co;2-z

  日期：1999.3

  A novel series of 3-carbamoylethynyl-2-carboxyindoles, antagonists acting at the strychnine-insensitive glycine binding site associated with the NMDA receptor, has been synthesised. This new versatile approach involves the introduction of a 2-chloroethenyl moiety in position C-3 with subsequent derivatisation of the terminal carboxyl group, followed by an unusual elimination of HCl to afford the ethynyl functionality. This novel series of glycine antagonists was evaluated in terms of in vitro affinity at the glycine bindings site and the most potent compound was tested in vivo in the NMDA-induced convulsions model in mice.